Plymouth Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Plymouth Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Plymouth vacation package. Look for places to stay in Litchfield Historic District, which is great for shopping, dining and history. If sightseeing is on the agenda during your trip to Plymouth, check out popular attractions like Black Rock State Park. Stop daydreaming and start traveling. Browse the range of options on Expedia today and put your Plymouth vacation plans into action!

Top Plymouth Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.6/10 Excellent! (1,041 reviews)
The Property was clean and the staff were nice.

Reviewed on Jul. 14, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.8/10 Excellent! (1,703 reviews)
Compact room but clean, comfortable. Good price, includes breakfast.

Reviewed on Jul. 10, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
8.4/10 Very Good! (1,015 reviews)
Clean room, friendly staff. We stayed Sat-Mon and while the hotel was great, there was quite a bit of noise from the bars & partiers on the street. There was a panel under our window that let in all the sound. If I didn't have my earplugs, sleep would have been a struggle. Not being used to the downtown environment, we didn't feel very safe in the area and chose to drive most of the time when leaving the hotel. The restaurant on the 19th floor was great for our Monday breakfast with a varied menu and well-presented and delicious food.

Reviewed on Jul. 12, 2025

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.2/10 Very Good! (1,001 reviews)
Staff Was very friendly and helpful. Property was very well maintained and very clean . Great stay will be back Very soon.

Reviewed on Jul. 13, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (831 reviews)
Very nice convenient to Yale museums.

Reviewed on Jul. 9, 2025

Ready to book your vacation to Plymouth?

 

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Plymouth Hotel Deals

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth
10/10 Exceptional! (33 reviews)
Visit with family
"The house is beautifully appointed with an incredible view of the lake ! The backyard was a perfect place to gather with family and have an amazing view. The owners are so responsive! Great beds and linens. Everything you need for a peaceful cozy oasis."

Reviewed on May 22, 2025

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Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Cozy Lakefront Bungalow w firepit/dock/kayaks
Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth
9.8/10 Exceptional! (26 reviews)
Lake retreat
"Cozy and peaceful property. Well maintained and spacious. Everything you need and more. Located in a wonderful neighborhood and close to restaurants and attractions. This little bungalow will one we love to return to. Thank you for sharing it with us."

Reviewed on Jul. 5, 2025

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Cozy Lakefront Bungalow w firepit/dock/kayaks
Wyndham Southbury
Wyndham Southbury
3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jul 27 to Jul 28
CA $127
CA $146 total
Jul 27 - Jul 28
includes taxes & fees
8/10 Very Good! (1,012 reviews)
"The staff there was very helpful. The cleaning staff was excellent also. The rooms were beautiful. We loved the pool. Thank you to everyone."

Reviewed on Jul. 10, 2025

Wyndham Southbury
See all 642 properties in Plymouth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Plymouth vacation package cost?
You'll find cheap prices from CA $648 on Expedia for your Plymouth break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Plymouth costs.
What are the cheapest months to go to Plymouth?
You're likely to find reduced prices and greater availability in January, February and March. Check out our cheap Plymouth vacation packages and you could get some great off-season discounts.
How many days is enough for Plymouth?
The ideal length of your Plymouth vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to hit all the main sights and discover some hidden gems along the way.
How to find the best Plymouth package deals?
Use Expedia's filter tool to help you find some of the best Plymouth package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Plymouth package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Plymouth vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the freedom to create a customized Plymouth vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Plymouth?
If you're planning a spur-of-the-moment Plymouth trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Plymouth?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Plymouth.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Plymouth.
  3. Decide how long to go away for: Now that you're more familiar with Plymouth, you can work out the ideal length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Plymouth vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.